Skip to main content

Polynucleotide Analogues

  • Chapter
  • First Online:

Part of the book series: Advances in Polymer Science ((POLYMER,volume 153))

Abstract

Nucleic acids (DNAs and RNAs) are biopolymers, called polynucleotides as polymers of nucleotides. They have purine or pyrimidine bases and sugar rings connected by phosphodiester linkages. Polynucleotide analogues (PNAs) with modified polymer backbones and/or modified nucleic acid bases have been studied as model polymers for natural nucleic acids. In spite of their structural simplicity, PNAs have shown the property of base-stacking along the synthetic polymer backbones and even interacted with natural nucleic acids through base-pairing. Since biological activities of natural nucleic acids are indebted greatly to base-base interactions, PNAs are expected to have certain types of biological activities. In this article the preparation methods, properties, and potential applications of PNAs are discussed.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Watson JD, Crick FHC (1953) Nature 171:737

    Article  CAS  Google Scholar 

  2. Inaki Y (1992) Prog Polym Sci 17:515

    Article  CAS  Google Scholar 

  3. Takemoto K, Inaki Y (1987) In: Takemoto K, Inaki Y, Ottenbrite RM (eds) Functional monomers and polymers. Marcel Dekker, New York, p 149

    Google Scholar 

  4. Overberger CG, Inaki Y (1979) J Polym Sci Chem Ed 17:1739

    Article  CAS  Google Scholar 

  5. Overberger CG, Inaki Y, Nambu Y (1979) J Polym Sci Chem Ed 17:1759

    Article  CAS  Google Scholar 

  6. Overberger CG, Chang JY (1989) J Polym Sci Chem Ed 27:3589

    Article  CAS  Google Scholar 

  7. Han MJ, Cho TJ, Chang JY (1996) Polynucleotide analogues. In: Salamone JC (ed) Polymeric materials encyclopedia. CRC, Boca Raton, vol 8, p 6402

    Google Scholar 

  8. Han MJ, Park SM (1990) Macromolecules 23:5295

    Article  CAS  Google Scholar 

  9. Han MJ, Lee CW, Kim KH, Lee SH (1992) Macromolecules 25:3528

    Article  CAS  Google Scholar 

  10. Han MJ, Park SM, Park JY, Yoon SH (1992) Macromolecules 25:3534

    Article  CAS  Google Scholar 

  11. Han MJ, Chang YS, Park JY, Kim KH (1992) Macromolecules 25:6574

    Article  CAS  Google Scholar 

  12. Han MJ, Kim KS, Cho TJ, Kim KH, Chang JY (1994) Macromolecules 27:2896

    Article  CAS  Google Scholar 

  13. Han MJ, Park SW, Cho TJ, Chang JY (1996) Polymer 37:667

    Article  CAS  Google Scholar 

  14. Han MJ, Lee GH, Cho TJ, Park SK, Kim JH, Chang JY (1997) Macromolecules 30:1218

    Article  CAS  Google Scholar 

  15. Hafird MH, Jones AS (1968) J Chem Soc (c) 2667

    Google Scholar 

  16. Nielsen PE, Haaima G (1997) Chem Soc Rev 73

    Google Scholar 

  17. Overberger CG, Morishima Y (1980) J Polym Sci Polym Chem Ed 18:1247

    Article  CAS  Google Scholar 

  18. Ludwick AG, Overberger CG (1982) J Polym Sci Polym Chem Ed 20:2123

    Article  CAS  Google Scholar 

  19. Chu VP, Overberger CG (1986) J Polym Sci Polym Chem Ed 24:2657

    Article  CAS  Google Scholar 

  20. Lan M-J, Overberger CG (1987) J Polym Sci Polym Chem Ed 25:1909

    Article  CAS  Google Scholar 

  21. Overberger CG, Kikyotani S (1983) J Polym Sci Polym Chem Ed 21:525

    Article  CAS  Google Scholar 

  22. Ishikawa T, Inaki Y, Takemoto K (1978) Polym Bull 1:85

    CAS  Google Scholar 

  23. Anand N, Murthy NSRK, Naider F, Goodman M (1971) Macromolecules 4:564

    Article  CAS  Google Scholar 

  24. Overberger CG, Chang JY, Gunn VE (1989) J Polym Sci Chem Ed 27:99

    Article  CAS  Google Scholar 

  25. Overberger CG, Chang JY (1989) J Polym Sci Chem Ed 27:4013

    Article  CAS  Google Scholar 

  26. Scita T, Yamauchi K, Kinoshita M, Imoto M (1972) Macromol Chem 154:263

    Article  Google Scholar 

  27. Scita T, Yamauchi K, Kinoshita M, Imoto M (1973) Macromol Chem 164:15

    Article  Google Scholar 

  28. Han MJ, Kim KH, Cho TJ, Choi KB (1990) J Polym Sci Chem Ed 28:2719

    Article  CAS  Google Scholar 

  29. Han MJ, Choi KB, Chae JP, Hahn BS (1990) J Bioactive Compatible Polym 5:80

    Article  CAS  Google Scholar 

  30. Han MJ, Choi KB, Chae JP, Hahn BS (1990) Bull Korean Chem Soc 11:154

    CAS  Google Scholar 

  31. Morris CJOR (1976) Separation methods in biochemistry. Wiley, New York

    Google Scholar 

  32. Tinoco I Jr (1961) J Am Chem Soc 83:5047

    Article  Google Scholar 

  33. Rhodes W (1961) J Am Chem Soc 83:3609

    Article  CAS  Google Scholar 

  34. Bush CA (174) In: Ts’o POP (ed) Basic principles in nucleic acid chemistry. Academic, New York, vol II, chap 2

    Google Scholar 

  35. Browne DT, Eisinger J, Leonard NJ (1968) J Am Chem Soc 90:7302

    Article  CAS  Google Scholar 

  36. Inaki Y, Renge T, Kondo K, Takemoto K (1975) Makromol Chem 176:2683

    Article  CAS  Google Scholar 

  37. MacDonald JR, Echols WE, Price TR, Fox RB (1972) J Chem Phys 57:1746

    Article  Google Scholar 

  38. Iyata T, Ochiai H, Ueda K, Imamura A (1993) Macromolecules 26:6021

    Article  Google Scholar 

  39. Riley M, Mailing B, Charmberin MJ (1966) J Mol Biol 20:359

    Article  CAS  Google Scholar 

  40. Stevens CL, Felsenfeld G (1964) Biopolymers 2:293

    Article  CAS  Google Scholar 

  41. Zmudzka B, Bollum FJ, Shugar D (1969) J Mol Biol 46:169

    Article  CAS  Google Scholar 

  42. Blake RD, Massoulie J, Fresco JR (1967) J Mol Biol 30:291

    CAS  Google Scholar 

  43. Sequaris J-M, Koglin E, Valenta P, Nurnberg HW (1981) Ber Bunsen-Ges Phys Chem 85:512

    CAS  Google Scholar 

  44. Cotton TM (1988) In: Clark RJH, Hester RE (eds) Spectroscopy of surfaces. Wiley, New York, p 91

    Google Scholar 

  45. Brabec V, Niki K (1985) Biophys Chem 23:63

    Article  CAS  Google Scholar 

  46. Kaye H (1970) J Am Chem Soc 92:5777

    Article  CAS  Google Scholar 

  47. Akashi M, Okamoto T, Inaki Y, Takemoto K (1979) J Polym Sci Chem Ed 17:905

    Article  CAS  Google Scholar 

  48. Takemoto K, Tahara H, Yamada A, Inaki Y, Ueda N (1973) Makromol Chem 169:327

    Article  CAS  Google Scholar 

  49. Doel MT, Jones AS, Walker RT (1974) Tetrahedron 30:2755

    Article  CAS  Google Scholar 

  50. Buttrey JD, Jones AS, Walker RT (1975) Tetrahedron 31:73

    Article  CAS  Google Scholar 

  51. Draminski M, Pitha J (1978) Makromol Chem 179:2195

    Article  CAS  Google Scholar 

  52. Ishikawa T, Inaki Y, Takemoto K (1978) Polym Bull 1:215

    CAS  Google Scholar 

  53. Takemoto K, Yahara H, Yamada A, Inaki Y, Ueda N (1973) Makromolek Chem 169:327

    Article  CAS  Google Scholar 

  54. Alberts B, Bray D, Lewis J, Raff M, Roberts K, Watson JD (1994) Molecular biology of the cell, 3rd edn. Garland, New York

    Google Scholar 

  55. Uhlmann E, Peyman A (1990) Chem Rev 90:543

    Article  CAS  Google Scholar 

  56. Nielsen PE, Egholm M, Berg RH, Buchardt O (1991) Science 254:1497

    Article  CAS  Google Scholar 

  57. Egholm M, Buchardt O, Nielsen PE, Berg RH (1992) J Am Chem Soc 114:1895

    Article  CAS  Google Scholar 

  58. Egholm M, Buchardt O, Nielsen PE, Berg RH (1992) J Am Chem Soc 114:9677

    Article  CAS  Google Scholar 

  59. Egholm M, Buchardt O, Christensen L, Behrens C, Freier SM, Driver D, Berg RH, Kim SK, Norden B, Nielsen PE (1993) Nature 365:566

    Article  CAS  Google Scholar 

  60. Kim SK, Nielsen PE, Egholm M, Buchardt O, Berg RH, Norden B (1993) J Am Chem Soc 115:6477

    Article  CAS  Google Scholar 

  61. Wittung P, Nielsen PE, Buchardt O, Egholm M, Norden B (1994) Nature 368:561

    Article  CAS  Google Scholar 

  62. Wittung P, Eriksson M, Lyng R, Nielsen PE, Nordén B (1995) J Am Chem Soc 117:10,167

    Article  CAS  Google Scholar 

  63. Wittung P, Nielsen PE, Nordén B (1997) J Am Chem Soc 119:3189

    Article  CAS  Google Scholar 

  64. Cantin M, Schütz R, Leumann CJ (1997) Tetrahedron Lett 38:4211

    Article  CAS  Google Scholar 

  65. Kosynkina L, Wang W, Liang YC (1994) Tetrahedron Lett 35:5173

    Article  CAS  Google Scholar 

  66. Goodnow RA Jr, Richou A, Tarn S (1997) Tetrahedron Lett 38:3195

    Article  CAS  Google Scholar 

  67. Goodnow RA Jr, Tarn S, Pruess DL, McComas WW (1997) Tetrahedron Lett 38:3199

    Article  CAS  Google Scholar 

  68. Howarth NM, Wakelin LPG (1997) J Org Chem 62:5441

    Article  CAS  Google Scholar 

  69. Kita Y, Uno T (1981) J Polym Sci Polym Chem Ed 19:477

    Article  CAS  Google Scholar 

  70. Suda Y, Inaki Y, Takemoto K (1984) J Polym Sci Polym Chem Ed 22:623

    Article  CAS  Google Scholar 

  71. Kunkel TA (1984) Proc Natl Acad Sci USA 81:1494

    Article  CAS  Google Scholar 

  72. Vousden KH, Bos JL, Marsheall CJ, Phillips DH (1986) Proc Natl Acad Sci USA 83:1222

    Article  CAS  Google Scholar 

  73. Lindahl T, Nyberg B (1972) Biochemistry 11:3610

    Article  CAS  Google Scholar 

  74. Lindahl T, Andersson A (1972) Biochemistry 11:3618

    Article  CAS  Google Scholar 

  75. Lindahl T (1982) Annu Rev Biochem 51:61

    Article  CAS  Google Scholar 

  76. Drake JW, Baltz RH (1976) Annu Rev Biochem 45:11

    Article  CAS  Google Scholar 

  77. Shaaper RN, Leob LA (1981) Proc Natl Acad Sci USA 78:1773

    Article  Google Scholar 

  78. Han MJ, Cho TJ, Lee GH, Yoo KS, Park YD, Chang JY (1999) J Polym Sci Chem Ed 37:3361

    Article  CAS  Google Scholar 

  79. Garrett ER, Seydel JK, Sharpen AJ (1966) J Org Chem 31:2199

    Google Scholar 

  80. Shapiro R, Danzig M (1972) Biochemistry 11:23

    Article  CAS  Google Scholar 

  81. Shapiro R, Danzig M (1973) Biochim Biophys Acta 319:5

    CAS  Google Scholar 

  82. Cech TR (1990) Angew Chem Int Ed Engl 29:759

    Article  Google Scholar 

  83. Altman S (1990) Angew Chem Int Ed Engl 29:749

    Article  Google Scholar 

  84. Uhlenbeck OC (1987) Nature 328:596

    Article  CAS  Google Scholar 

  85. Cech TR (1986) Sci Amer 255:76

    Article  Google Scholar 

  86. Zuag AJ, Cech TR (1986) Science 231:470

    Article  Google Scholar 

  87. McSwiggen JA, Cech TR (1989) Science 244:679

    Article  CAS  Google Scholar 

  88. Cech TR (1987) Science 236:1532

    Article  CAS  Google Scholar 

  89. Brehm SL, Cech TR (1983) Biochemistry 22:2390

    Article  CAS  Google Scholar 

  90. Zaug AJ, Been MD, Cech TR (1986) Nature 324:429

    Article  CAS  Google Scholar 

  91. Bass BL, Cech TR (1984) Nature 308:820

    Article  CAS  Google Scholar 

  92. Guerrier-Takada C, Haydock K, Allen L, Altman S (1986) Biochemistry 25:1509

    Article  CAS  Google Scholar 

  93. Guerrier-Takada C, Gardiner K, Marsh T, Pace N, Altman S (1983) Cell 35:849

    Article  CAS  Google Scholar 

  94. Baer M, Altman S (1985) Science 228:999

    Article  CAS  Google Scholar 

  95. Sribivasan A, Reddy EP, Dunn CY, Aaronson SA (1984) Science 223:285

    Article  Google Scholar 

  96. Herschlag D, Cech TR (1990) Nature 344:405

    Article  CAS  Google Scholar 

  97. Robertson DL, Joyce GF (1990) Nature 344:467

    Article  CAS  Google Scholar 

  98. Han MJ, Macromolecules (in press)

    Google Scholar 

  99. Han MJ, Yoo KS, Cho TJ, Chang JY, Cha YJ, Nam SH (1997) Chem Comm 163

    Google Scholar 

  100. Han MJ, Yoo KS, Kim KH, Lee GH, Chang JY (1997) Macromolecules 30:5408

    Article  CAS  Google Scholar 

  101. Nagae S, Miyamoto T, Inaki Y, Takemoto K (1989) Polym J 21:19

    Article  CAS  Google Scholar 

  102. Nagae S, Suda Y, Inaki Y, Takemoto K (1989) J Polym Sci Polym Chem Ed 27:2593

    Article  CAS  Google Scholar 

  103. Inaki Y, Ebisutani K, Takemoto K (1986) J Polym Sci Polym Chem Ed 24:3249

    Article  CAS  Google Scholar 

  104. Inaki Y, Takemoto K (1988) J Macromol Sci Chem 25:757

    Article  Google Scholar 

  105. Moghaddam MJ, Hozumi S, Inaki Y, Takemoto K (1989) Polym J 21:203

    Article  CAS  Google Scholar 

  106. Moghaddam MJ, Hozumi S, Inaki Y, Takemoto K (1988) J Polym Sci Polym Chem 26:3297

    Article  CAS  Google Scholar 

  107. Haines DS, Strauss KI, Gillespie DH (1991) J Cell Biochem 46:9

    Article  CAS  Google Scholar 

  108. Torrence PF, DeClercq E (1990) Pharmacol Ther 2:1

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 2000 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Han, M.J., Chang, J.Y. (2000). Polynucleotide Analogues. In: Biopolymers · PVA Hydrogels, Anionic Polymerisation Nanocomposites. Advances in Polymer Science, vol 153. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-46414-X_1

Download citation

  • DOI: https://doi.org/10.1007/3-540-46414-X_1

  • Received:

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-67313-2

  • Online ISBN: 978-3-540-46414-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics